(2S)-2-amino-N-(3,5-dimethylphenyl)propanamide | 253867-84-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-amino-N-(3,5-dimethylphenyl)propanamide
• CAS: 253867-84-4
• 化学式: C₁₁H₁₆N₂O
• 分子量: 192.261
• InChiKey: HDMGAWAVSDMCJJ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-N-(3,5-dimethylphenyl)propanamide 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-butylamino-N-[1-((3,5-dimethylphenyl)carbamoyl)ethyl]-3,5-dinitrobenzamide
  参考文献：
  名称：

  The enantiomeric recognition of dihydropyrimidonic compounds by chiral selectors derived from 4- or 2-chloro-3,5-dinitrobenzoic acid

  摘要：

  Six new chiral packing materials for high performance liquid chromatography have been prepared from chiral selectors consisting of 4- or 2-chloro-3,5-dinitrobenzoic acid, L-alanine and different pi-donor aromatic units. Comparative tests of these newly prepared CSPs on separation efficiency for 13 racemic dihydropyrimidonic (DHPM) analytes have revealed the strong contribution of the pi-acceptor branching unit, as well as the important influence of the structure of the terminal pi-donor unit. The role of the terminal aromatic group is primarily to increase the rigidity of the selector structure. Comparisons of the data revealed that selectors bound on the silica gel could be preorganized during the process of chiral recognition, resulting in the similar enantioseparation properties for DHPM analytes on both types of CSPs. However, some other compounds, such as amino alcohol beta-agonists, exhibit very different enantioseparations. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.042
• 作为产物：
  描述：

  tert-butyl N-[(2S)-1-(3,5-dimethylanilino)-1-oxopropan-2-yl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2S)-2-amino-N-(3,5-dimethylphenyl)propanamide
  参考文献：
  名称：

  Enhanced gelation property due to intra-molecular hydrogen bonding in a new series of bis(amino acid)-functionalized pyridine-2,6-dicarboxamide organogelators

  摘要：

  A series of pyridine-2,6-dicarboxamide derivatives containing two alpha-amino acid pendant groups was prepared and characterized. Three of the synthesized compounds obtained from this series, all having aromatic amino acid side chains, were found to be excellent organo-gelators toward aromatic solvents (mgc similar to 10-20 mg/mL), alcoholic solvents (mgc similar to 4-15 mg/mL), and CCl4 ( mgc similar to 4-10 mg/mL). It was found that the intra-molecular hydrogen bonds between the pyridine dicarboxamide N-Hs and the pyridine N atom were the key structural elements for gel formation. This series of compounds represented one of the rare examples where both inter- and intra-molecular hydrogen bonds were needed for effective gel formation. FTIR, H-1 NMR, and CD spectroscopy revealed that both hydrogen bonding and pi-pi aromatic stacking were the driving forces for gelation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.037

文献信息

• The enantiomeric recognition of dihydropyrimidonic compounds by chiral selectors derived from 4- or 2-chloro-3,5-dinitrobenzoic acid
  作者：Ivana Gazić、Darko Kontrec、Andreja Lesac、Vladimir Vinković

  DOI：10.1016/j.tetasy.2005.01.042

  日期：2005.3

  Six new chiral packing materials for high performance liquid chromatography have been prepared from chiral selectors consisting of 4- or 2-chloro-3,5-dinitrobenzoic acid, L-alanine and different pi-donor aromatic units. Comparative tests of these newly prepared CSPs on separation efficiency for 13 racemic dihydropyrimidonic (DHPM) analytes have revealed the strong contribution of the pi-acceptor branching unit, as well as the important influence of the structure of the terminal pi-donor unit. The role of the terminal aromatic group is primarily to increase the rigidity of the selector structure. Comparisons of the data revealed that selectors bound on the silica gel could be preorganized during the process of chiral recognition, resulting in the similar enantioseparation properties for DHPM analytes on both types of CSPs. However, some other compounds, such as amino alcohol beta-agonists, exhibit very different enantioseparations. (C) 2005 Elsevier Ltd. All rights reserved.
• Enhanced gelation property due to intra-molecular hydrogen bonding in a new series of bis(amino acid)-functionalized pyridine-2,6-dicarboxamide organogelators
  作者：Hak-Fun Chow、Guo-Xin Wang

  DOI：10.1016/j.tet.2007.02.037

  日期：2007.7

  A series of pyridine-2,6-dicarboxamide derivatives containing two alpha-amino acid pendant groups was prepared and characterized. Three of the synthesized compounds obtained from this series, all having aromatic amino acid side chains, were found to be excellent organo-gelators toward aromatic solvents (mgc similar to 10-20 mg/mL), alcoholic solvents (mgc similar to 4-15 mg/mL), and CCl4 ( mgc similar to 4-10 mg/mL). It was found that the intra-molecular hydrogen bonds between the pyridine dicarboxamide N-Hs and the pyridine N atom were the key structural elements for gel formation. This series of compounds represented one of the rare examples where both inter- and intra-molecular hydrogen bonds were needed for effective gel formation. FTIR, H-1 NMR, and CD spectroscopy revealed that both hydrogen bonding and pi-pi aromatic stacking were the driving forces for gelation. (c) 2007 Elsevier Ltd. All rights reserved.